The proposed research will continue our efforts in development of mild catalytic stereoselective methods for C-C bond formation. In the preceding funding period, reductive coupling reactions were developed wherein C-C bond formation was accomplished under conditions which use a mild silane reducing agent. Our research in this area has largely concluded and we have begun to examine alternate methods for mild C-C bond formation under palladium catalysis. The palladium catalyzed process which we will develop will accomplish C-C bond formation under extraordinarily mild conditions and in a stereoselective fashion. The processes proposed herein will deliver fundamental chiral building blocks which are difficult to access with competitive methodologies. In addition to the methods developed, we will target a number of biologically and structurally interesting natural products. The synthesis endeavors will serve to challenge the efficacy of newly developed methodologies, will highlight their eventual utility to synthetic chemists, and will provide a framework to introduce new synthesis strategies.